Markets in Chicago the Weekend of Sep 25–27, 2026

Stumblday's hand-checked ranking of the best markets in Chicago the weekend of Sep 25–27, 2026: 1 pick, refreshed weekly.

1 picks · checked Sep 10

All weekendFri nightSaturdaySat nightSundaySun night

All Chicago Downtown, the Loop & West Loop Lincoln Park, Lakeview & Wrigleyville Logan Square, Wicker Park & Bucktown Pilsen, West Town & the West Side Hyde Park, Bronzeville & the South Side Andersonville, Uptown & Lincoln Square Evanston & Oak Park Far Suburbs

All Free Art Music Markets Outdoors Food Date night

#1

Randolph Street Market

1341 W. Randolph Street, Chicago, IL 60607, West Loop, Downtown, the Loop & West LoopJohn W. Taylor · Public domain · Wikimedia Commons

Sat, Sep 26, 2026 · 10:00am$5.00 – $100.00

Randolph Street Market

Hunt for vintage clothing, vinyl and antiques at Randolph Street Market’s indoor-and-outdoor September edition.

One Weekend Only

Submitted byStumblday Editors

#1Sat, Sep 26, 2026 · 10:00am · One Weekend Only

Randolph Street Market

1341 W. Randolph Street, Chicago, IL 60607, West Loop, Downtown, the Loop & West LoopJohn W. Taylor · Public domain · Wikimedia Commons

$5.00 – $100.00One Weekend Only

Randolph Street Market

Hunt for vintage clothing, vinyl and antiques at Randolph Street Market’s indoor-and-outdoor September edition.

More this weekend across Chicago

Chicago Gourmet 2026Harris Theater Rooftop, Downtown, the Loop & West Loop

Chicago Humanities Fall Festival Pilsen Day 2026National Museum of Mexican Art, Pilsen, West Town & the West Side

13th Annual Beverly Art WalkWestern Avenue in Beverly/Morgan Park, Hyde Park, Bronzeville & the South Side

Hyde Park Jazz Festival 2026Multiple Hyde Park venues, Hyde Park, Bronzeville & the South Side

Teddy Swims – The Ugly TourUnited Center, 1901 W Madison, Pilsen, West Town & the West Side

World Music Festival Chicago 2026Multiple Chicago venues